On-Site Onboarding Lead - Drive 30-Day Activation & NPS

Plum Benefits, LLC; Eastern Ontario; On-site; CAD 110,000 - 170,000; Full time

Job summary

Plum is seeking a senior onboarding leader to drive activation for our largest customers. You will own the onboarding journey from pre-sales through closeout, coordinating with account managers and insurers to ensure a seamless handoff and value realization.

With 7–8 years total experience and strong stakeholder management, you will guide training and consult on product best practices, using AI to elevate the customer activation experience.

Qualifications

• Experience leading onboarding teams for enterprise customers.
• Ability to align cross-functional stakeholders to drive activation.
• Interest in AI and using data to improve customer journeys.

Responsibilities

• Lead onboarding for top customers from pre-sale to closeout.
• Partner with Account Managers and Insurers to ensure smooth handoffs.
• Define timelines and drive activation milestones in 30-day window.
• Report metrics and customer feedback to spot improvement opportunities.
• Deliver scalable training sessions tailored to customer maturity.

Skills

Onboarding management

Stakeholder management

AI interest

Project management

Customer empathy

Strong communication

Job description

Plum is seeking a senior onboarding leader to drive activation for our largest customers. You will own the onboarding journey from pre-sales through closeout, coordinating with account managers and insurers to ensure a seamless handoff and value realization.

With 7–8 years total experience and strong stakeholder management, you will guide training and consult on product best practices, using AI to elevate the customer activation experience.